Chlorotrimethylsilane → HCID 13651882, compound

HRID 1981864Notes

Reaction equation

HRID 1981864 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11]([OH:13])[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C[Si](Cl)(C)C.[CH:26](=[O:30])/[CH:27]=[CH:28]/[CH3:29]>C(Cl)(Cl)Cl>[OH:12][P:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH:28]([CH3:29])[CH2:27][CH:26]=[O:30])=[O:13]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 447466CrotonaldehydeHCID 132746654-Phenylbutylphosphonous acid

Product 1

HCID 13651882HCID 13651882, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-phenylbutyl phosphonous acid (0.5 g, 0.0025 mole) in chloroform (15 ml) was added triethylamine (0.77 ml, 0.005 mole), trimethyl silylchloride (0.70 ml, 0.005 mole) and crotonaldehyde (0.23 ml, 0.0025 mole). The reaction mixture was stirred at reflux temperature for 18 hours. The chloroform was removed in vacuo. The residue was diluted with ether and extracted with 5% NaHCO3 solution. The aqueous layer was acidified with concentrated HCl and extracted twice with ether and once with EtOAc. The combined organic phase was washed with water and brine, dried over anhydrous sodium sulphate and the organic solvent removed on a rotavap to produce the title compound as a solid which was dissolved in CH3OH; ether and hexane were added until turbidity. The mixture was kept in a freezer overnight, yield 0.099, m.p. 138° C.

Workup

  1. temperatureat reflux temperature for 18 hours
  2. customThe chloroform was removed in vacuo
  3. additionThe residue was diluted with ether
  4. extractionextracted with 5% NaHCO3 solution
  5. extractionextracted twice with ether and once with EtOAc
  6. washThe combined organic phase was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe organic solvent removed on a rotavap

Sources & evidence

ORD record
ord-6491e7bb8396487192183828f4e3186a
Source dataset
uspto-grants-1986_06
Patent number
US04594199

Reaction notes

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